4-[5-(4-Chloro­phen­yl)-3-methyl-1H-pyrazol-1-yl]benzene­sulfonamide

Muhammad A Farrukh; Shaaban K Mohamed; Maqsood Ahmed; Adel A Marzouk; Samir M El-Moghazy

doi:10.1107/S1600536813002134

. 2013 Jan 26;69(Pt 2):o295–o296. doi: 10.1107/S1600536813002134

4-[5-(4-Chlorophenyl)-3-methyl-1H-pyrazol-1-yl]benzenesulfonamide

Muhammad A Farrukh ^a, Shaaban K Mohamed ^b,^c, Maqsood Ahmed ^a,^*, Adel A Marzouk ^d, Samir M El-Moghazy ^e

PMCID: PMC3569817 PMID: 23424563

Abstract

In the title compound, C₁₆H₁₄ClN₃O₂S, the dihedral angle between the benzene and pyrazole rings is 52.75 (2)°, while that between the pyrazole and 4-chlorophenyl rings is 54.0 (3)°. The terminal sulfonamide group adopts an approximately tetrahedral geometry about the S atom with a C—S—N angle of 108.33 (10)°. In the crystal, pairs of N—H⋯N hydrogen bonds lead to the formation of inversion dimers. These dimers are linked via a second pair of N—H⋯N hydrogen bonds and C—H⋯O interactions, forming a two-dimensional network lying parallel to the bc plane. The two-dimensional networks are linked via C—H⋯Cl interactions, forming a three-dimensional structure.

Related literature

For the use of pyrazoles in metal-organic chemistry, see: Mukherjee (2000 ▶); Halcrow (2009 ▶). For the synthesis and pharmaceutical applications of pyrazole compounds, see, for example: Ranatunge et al. (2004 ▶); Szabo et al. (2008 ▶); Bekhit & Abdel-Aziem (2004 ▶); Bekhit et al. (2006 ▶); Rostom et al. (2003 ▶); Gökhan-Kelekçi et al. (2007 ▶); Lin et al. (2007 ▶); El-Moghazy et al. (2012 ▶); Sakya et al. (2008 ▶); Shen et al. (2004 ▶).

Experimental

Crystal data

C₁₆H₁₄ClN₃O₂S
M _r = 347.81
Monoclinic,
a = 15.878 (5) Å
b = 8.209 (5) Å
c = 12.953 (5) Å
β = 91.016 (5)°
V = 1688.1 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 296 K
0.33 × 0.32 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: analytical (SADABS; Bruker, 2009 ▶) T _min = 0.890, T _max = 0.938
17257 measured reflections
3462 independent reflections
2594 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.115
S = 1.03
3462 reflections
217 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(23.8KB, cif)}

Crystal structure: contains datablock(s) I, global_Publ_Block. DOI: 10.1107/S1600536813002134/sj5296sup1.cif

e-69-0o295-sup1.cif^{(23.8KB, cif)}

Click here for additional data file.^{(169.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002134/sj5296Isup2.hkl

e-69-0o295-Isup2.hkl^{(169.8KB, hkl)}

Click here for additional data file.^{(5.9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813002134/sj5296Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2N1⋯N3ⁱ	0.82 (2)	2.20 (2)	3.010 (3)	169 (2)
N1—H1N1⋯N3ⁱⁱ	0.84 (3)	2.33 (3)	3.157 (3)	167 (3)
C5—H5⋯O2ⁱⁱⁱ	0.93	2.48	3.169	131
C3—H3⋯Cl1^iv	0.93	2.93	3.602	130

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

GC University is gratefully acknowledged for use of the X-ray diffraction facility. The authors are also thankful to Manchester Metropolitan University and Alazhar University for supporting this study.

supplementary crystallographic information

Comment

Pyrazoles and related compounds are common molecules used in coordination or organometallic chemistry as bridging ligands, utilizing the ring positions of the two N atoms (Mukherjee, 2000; Halcrow, 2009). In addition, pyrazole derivatives represent an important class of biologically and pharmacologically active molecules. Several pyrazole compounds have been reported to be potential therapeutic agents for the treatment of inflammation (Ranatunge et al., 2004; Szabo et al., 2008; Bekhit & Abdel-Aziem 2004; Bekhit et al., 2006) including the marketed selective COX-2 drug, Celecoxib, that have been shown to be well tolerated with reduced gastrointestinal side effects (Sakya et al., 2008). Moreover, various substituted pyrazoles were reported to possess antitumor properties (Rostom et al., 2003; Lin et al., 2007). Other pyrazoles were used for treating Alzheimer's disease (Gökhan-Kelekçi et al., 2007) and acquired immunodeficiency syndrome (AIDS) (Shen et al., 2004; El-Moghazy et al., 2012).

The molecular assembly is built on the basis of intermolecular N—H···N type hydrogen bonds. The N3 atom on one side accepts a H1N1 atom from a neighbouring atom at a distance of 2.33 (3) Å and also accepts a H2N1 atom from a molecule on the opposite side at a distance of 2.20 (2) Å. There is a weak C–H···O type intermolecular hydrogen bond where the C5 atom donates its H atom to the O2 of the sulfonamide group at a distance of 2.48 Å and C—H—O angle of 130.8°. The molecule is also involved in the formation of a pair of weak intermolecular inversion related C3—H3···Cl1 hydrogen bonds where in one case the Cl1 atom accepts a H atom from a neighbouring molecule while in return, the C3 atom donates its H3 atom to the same molecule. The C–H···Cl distance in both cases is 2.93 Å and C—H—Cl angle is 130.0°.

Experimental

A mixture of 1 mmol (197 mg) 1-(4-chlorophenyl)butane-1,3-dione, 1 mmol (224 mg) 4-hydrazinylbenzenesulfonamide hydrochloride, 82 mg sodium acetate and 60 mg glacial acetic acid in 50 ml e thanol was stirred at room temperature for 24 h. The mixture was filtered off and the filtrate was concentrated under vacuum to deposit the solid product which was collected, dried and recrystallized from ethanol to afford a very good yield (80%) of high quality crystals suitable for X-ray diffraction (498 – 499 K).